98-74-8 Usage
Description
4-Nitrobenzenesulfonyl chloride is an organic compound that serves as a versatile reagent and intermediate in various chemical reactions and synthesis processes.
Uses
Used in Pharmaceutical Synthesis:
4-Nitrobenzenesulfonyl chloride is used as an intermediate for the synthesis of pharmaceuticals such as foscmprenavir, darunavir, and amprenavir. It plays a crucial role in the preparation of N-nosyl-alpha-amino acid for peptide synthesis, which is essential for the development of new drugs and therapeutic agents.
Used in Carbohydrate Chemistry:
In carbohydrate chemistry, 4-nitrobenzenesulfonyl chloride is utilized for stereoselective α-glucosylation of partially protected carbohydrates. This process involves the use of silver tri-fluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine, enabling the formation of specific carbohydrate structures with potential applications in drug design and development.
Used in Coordination Chemistry:
4-Nitrobenzenesulfonyl chloride is employed in the synthesis of coordination compounds, such as [Cu(bipy)2Cl](nbs) (1) (bipy = 2,2'-bipyridine, nbs = 4-nitrobenzenesulfonate). These compounds have potential applications in various fields, including catalysis, materials science, and supramolecular chemistry.
Used in Sulfonamide Synthesis:
4-Nitrobenzenesulfonyl chloride is used in the synthesis of hydroxylamines of sulfadiazine and sulfamethoxazole, which are important classes of antibiotics. This reagent contributes to the development of new antimicrobial agents to combat resistant bacterial strains.
Used in Peptide Synthesis:
In the field of peptide synthesis, 4-Nitrobenzenesulfonyl chloride is used in the preparation of N-nosyl-α-amino acids, which are key building blocks for the assembly of peptide sequences. This reagent facilitates the synthesis of peptides with specific properties and functions, finding applications in drug discovery, biochemistry, and biotechnology.
Overall, 4-Nitrobenzenesulfonyl chloride is a valuable chemical reagent with diverse applications across various industries, including pharmaceuticals, carbohydrate chemistry, coordination chemistry, sulfonamide synthesis, and peptide synthesis. Its versatility and reactivity make it an essential component in the development of new compounds and materials with potential applications in healthcare, materials science, and other fields.
Flammability and Explosibility
Notclassified
Check Digit Verification of cas no
The CAS Registry Mumber 98-74-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 98-74:
(4*9)+(3*8)+(2*7)+(1*4)=78
78 % 10 = 8
So 98-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H4ClNO4S/c7-13(11,12)6-3-1-5(2-4-6)8(9)10/h1-4H
98-74-8Relevant articles and documents
Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information, p. 20543 - 20550 (2021/08/12)
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
Sohrabnezhad, Samira,Bahrami, Kiumars,Hakimpoor, Farahman
, p. 256 - 264 (2019/02/06)
In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.
Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
, p. 3051 - 3057 (2016/04/26)
A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
